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Asymmetric Hydrogenation of Racemic α-Aryl-β-ethoxycarbonyl Cyclopentanones via Dynamic Kinetic Resolution and Its
Ying Xiong1, Han Lin1, Chang-Liang Zhu1
1State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Abstract:
An efficient asymmetric hydrogenation of racemic α-aryl-β-ethoxycarbonyl cyclopentanones via dynamic kinetic resolution is reported. Via catalysis by a chiral iridium Ir-SpiroPAP catalyst, a range of racemic α-aryl-β-ethoxycarbonyl cyclopentanones were hydrogenated to the corresponding ester-functionalized chiral 2-arylcyclopentanols with three contiguous stereocenters in high yields with excellent enantio- and diastereoselectivities. This method was successfully applied in the enantioselective synthesis of cyclopentane-based γ-amino ester/alcohol derivatives and phenylpropanoid (+)-burmaniol A.
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